My $100,000 bet on Chris Rock

Nobody on this site knows that telling a story about Chris Rock helped me earn over $100,000 in scholarship money to attend college.

During senior year of high school, my parents — immigrants who raised 4 kids and didn't have money to send us to college — encouraged us to apply to every scholarship we could find. Since I'm a big weirdo, I built a system that allowed me to apply to over 60 scholarships in a few weeks. (I've detailed parts of the system I used to get so many college scholarships.)

The largest scholarship I received had an extensive application process. First, you filled out an application with a hand-written essay, transcript, reference letter, and photo.

Then, if you were selected as a finalist, you were invited to the foundation's mansion. I had no idea about what I was going to encounter as I walked up the grand porch with my dad.

As we got to the door, a very serious woman looked at my dad, frowned, said, "You can wait here," and CLOSED THE DOOR ON MY DAD'S FACE. As she ushered me inside, I was too nervous to laugh at my dad standing outside, very confused.

Then she took me into a small room and handed me a piece of paper. "We'd like you to write an essay," she said. "You have 30 minutes."

I looked at the essay prompt. "If you could have dinner with anyone, living or dead, who would it be and why?"

Classic prompt. So I started thinking.

Nelson Mandela? Eh…it would be the "logical" choice, but honestly, dinner with Mandela wouldn't be that exciting for a 17-year-old kid.

President Clinton? Would be cool to brag about…but what would we really talk about?

At this point, it's about 3 minutes in to my writing time. I knew I could write some BS about Mandela or the President, but I would sound like every other candidate. Plus, I really didn't want to meet them.

And then I got it: Chris Rock.

At 17, I was a huge fan of his, I'd watched all his specials, and I could recite his jokes in my sleep. But I thought that much of what people thought about him was superficial.

And so I started to write. I wrote about how he is perceived as simply a comedian, but is actually a highly astute social commentator. How his jokes reveal the things we want to say, but we can't articulate — or we're afraid to.

I decided to go all-in.

I described one of his jokes — a story about a black woman's hands shaking as she buys groceries, hoping there's enough money in the account — which sounds aggressive (and is) but is actually a deep, subtle commentary. In the essay, I deconstructed the joke. What could be offensive was actually examining racial attitudes that our society holds. And since we can't discuss these attitudes intellectually, his comedy distills, simplifies, and reflects our attitudes, allowing us to have a shared experience around the elephants in the room.

I finished up the essay with a couple minutes to spare and handed it to the lady when she returned.

A few minutes later, I was shown into the interview room, where 6 interviewers faced me. The lady had taken my essay, made photocopies, and given copies to each of the interviewers, who had read it and were ready to discuss it with me.

"So," one of them said gravely, "tell us why you chose Mr. Rock."

And later, when I discovered that I had won over $100,000 in college scholarship money from this foundation, I thought back on that essay.

Choosing Chris Rock wasn't the inspired choice of a future entrepreneur. It was a nervous kid in a room who really believed in something. I later heard that one of my friends wrote about Watson and Crick (who discovered the double-helix structure of DNA). Which essay would you rather read? Who would you believe is genuinely interested in the topic? Who took a bigger risk?

When it comes to risks, most people look at them as an "all or nothing" bet. But as I demonstrate in my example of testing responses in bars, you can use testing, and other techniques, to mitigate risk…and make little bets.

I also have one more story about Chris Rock. It's about taking risks, and it's told by my friend Peter Sims, who just wrote the new book, Little Bets.

Peter — take it away.

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Peter Sims: Chris Rock's Little Bets

The following post is an exclusive excerpt from "Little Bets: How Breakthrough Ideas Emerge from Small Discoveries," by bestselling author and former venture capitalist Peter Sims. While there is no doubt Chris Rock has got great talent, his genius comes from his approach, that we can all learn from to do anything new well. The routines he rolls out on HBO and global tours are the result of what he has learned from thousands of little bets, nearly all of which fail.

In gearing up for his latest global tour, Rock made between forty and fifty appearances at small comedy clubs. His early performances can be painful to watch. Jokes will ramble, he'll lose his train of thought and need to refer to his notes, and some audience members sit with their arms folded, noticeably unimpressed. The audience will laugh about his flops—laughing at him, not with him.

Developing an hour-long act takes even top comedians like Rock from six months to a year. If comedians are serious about success, they get on stage every night they can, especially when developing new material. They typically do so at least five nights per week, sometimes up to seven, and sweat over every element and word. And the cycle repeats, day in, day out. (Writers for the Onion suggest roughly six hundred possibilities for eighteen headlines each week, a 3 percent success rate.)

By the time Rock reaches a big show — say an HBO special or an appearance on Letterman — he's flawless.

What we see on TV is not effortless genius. There's a method to the madness. It's the outgrowth of a brilliant approach, which includes: Think about what you can afford to lose, rather than what you can expect to gain. Just as Chris Rock doesn't plan or try to predict which jokes will work and which won't before trying them.

Learn a lot from a little. Rock watches the audience body language closely, especially the die-hard regulars who typically sit in the center of the room. Seeking out a small group of these active users with little bets is a proven way to tap into unique insights and desires.

Learn a little bit from a lot of people. Comedians like Rock and Jerry Seinfeld constantly seek out new ideas and insights by carefully observing what's going on in the world, whether it's standing in line at Starbucks, talking with taxi cab drivers, or going to events. They get out of the office.

Improvise, test, iterate, and repeat. It takes comedians like Rock six months to a year to develop an hours worth of material. They must persevere and learn to develop what Stanford social psychologist Dr. Carol Dweck calls a "growth mindset," to be able to overcome setbacks.

It all begins with one little bet. What will yours be?

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Peter's latest book, Little Bets, is available through all major booksellers. You can find more at his website, including a free excerpt.

Note from Ramit: The concept of "little bets" has changed many iwillteachyoutoberich readers' lives by challenging their ideas of what risk is, and how they can use small tests to change their behavior. Most people think that top performers like Chris Rock are simply "geniuses" — an easy label that completely overlooks the thousands of little bets they make in their lifetime. By adopting their systematic processes, you can leapfrog your peers to dramatically higher performance. While natural talent matters, it's not about being a genius — it's about building a system to methodically test your assumptions and performance. This is a great book that's worth your time.